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A $30,000 Mistake

John Urban  |  Jul 4, 2026

IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income.

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Close to Everything I Need

Dennis Friedman  |  Jun 20, 2026

I DON’T HAVE MANY regrets in life. But there is one conversation with my mother that I wish I had never had. It was about moving her into an assisted living facility. She was in her 90s, and I thought it would be best for both of us.
My mother would receive better care, and I could take much-needed breaks. She could even keep her house and spend time there when I was with her.
It seemed like a middle-of-the-road approach to providing care.

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The Humbling Side of Aging

Dennis Friedman  |  May 30, 2026

WHEN I STARTED writing for HumbleDollar, Jonathan gave me some simple but important advice: “Don’t brag about your financial situation. You want readers to like you.” Perhaps that’s one of the reasons he named his financial site HumbleDollar.
I try to follow this advice not only regarding money, but in other aspects of my life. I know how fleeting things can be—especially when it comes to health. Life can change on a dime. It can humble you.

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Retirement Accounts

Bogdan Sheremeta  |  May 16, 2026

I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.

There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.
Most people today will likely live well beyond age 59½.

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Slow on the Draw

Edmund Marsh  |  May 9, 2026

RETIREMENT IS LIFE’S most expensive purchase. During our working years, we deprive our present selves of immediate pleasure by refusing to spend money for nicer cars, a bigger house or a vacation to boast about. Instead, we squirrel away those saved dollars with an eye toward keeping the future us fed, clothed and living indoors. 
At age 64, after decades of choosing to save and invest a large chunk of each paycheck, rather than spend it,

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Sector Fund by Stealth

Mark Crothers  |  Mar 7, 2026

I’VE RECENTLY MADE the most significant change to my own portfolio in thirty five years. For the first time I’ve moved away from pure market-cap investing, tilting meaningfully toward Europe and Southeast Asia and bringing my US technology concentration down to around fifteen percent.
I’m retired. I don’t need to chase the outperformance that concentration might deliver, and I don’t need the potential volatility that comes with it. This is a personal position rather than any kind of recommendation;

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Tax Smart Retirement

Adam M. Grossman  |  Mar 7, 2026

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,

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Value of Waiting

Dennis Friedman  |  Feb 7, 2026

I WAS THINKING ABOUT Jonathan the other day on my morning walk, which happens more often than you might think. It’s hard not to think about him when you have HumbleDollar coasters in your living room and a HumbleDollar shopping bag in your car that you use for groceries. My wife confiscated the HumbleDollar cup I had been using for my morning tea, and it now has a new home in our bathroom holding her toothbrush and toothpaste.

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Early Retirement

Bogdan Sheremeta  |  Jan 17, 2026

MY COWORKER RECENTLY retired. He is 50 years old and has been with the company for over 25 years.
The company offers a decent 401(k) match (100% match on 6% of your salary) along with other great benefits.
In his case, how can he generate income? How can you retire early if most of your assets are in retirement plans?
Most tax-advantaged accounts have restrictions on withdrawals, but there are a few strategies that many people don’t know of:
 

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What’s Really On My Mind

Dennis Friedman  |  Dec 3, 2025

MY RETIREMENT HAS been wonderful so far. Honestly, sometimes I have to stop and remind myself how lucky I am. Rachel and I have our health and enjoy each other’s company, which is not always true when a couple retires. However, there are four things that concern me as I reach my mid-70s.
Loneliness
I tried calling Mark, my old high school friend, a couple of weeks ago, and I haven’t heard from him.

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How Not To Invest

Adam M. Grossman  |  Oct 11, 2025

BARRY RITHOLTZ’S NEW BOOK, How Not to Invest, offers investors a cautionary tale—many of them, in fact.
Ritholtz has been in and around the investment industry for more than 30 years—as a trader, a journalist and, most recently, as cofounder of a wealth management firm. 
In short, he is no stranger to Wall Street. His conclusion? It can be a minefield.
Bad actors like Charles Ponzi and Bernie Madoff are well known.

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Managing Concentration Risk

Adam M. Grossman  |  Oct 4, 2025

LARRY ELLISON, THE 81-YEAR-OLD cofounder of Oracle Corporation, recently became the world’s wealthiest person.
Oracle, a software company, isn’t nearly as large as its peers. So how did Ellison’s net worth manage to surpass that of Bill Gates, Jeff Bezos and the founders of other much larger companies?
The answer is simple: In the nearly 50 years since Oracle’s founding, Ellison has almost never sold a share of his company’s stock. According to an analysis by Smart Insider,

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What They Don’t Tell You About Retirement: Part 2 – Grandchildren Are Expensive

Mark Crothers  |  Sep 4, 2025

I know I and many others mockingly complain in a joking manner about our grandkids costing us a “fortune” when they visit—but with no malice intended, did you actually consider these costs when crafting your retirement spending plan?
I certainly never thought about this; it didn’t even cross my mind. Maybe I’m being too generous, or perhaps I’ve had a run of bad luck. In recent months, my granddaughter dropped an iPad, requiring a replacement, and my grandson accidentally let a toy car slip from his hand while spinning around,

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Dealing with a reduction in Social Security benefits. Is there a backup plan?

R Quinn  |  Aug 26, 2025

A recent post on the Forum raised the issue of dealing with a cut in Social Security benefits – hopefully an unlikely or very temporary event. However, something still worth planning for. 
If the status of SS is not fixed, around 2033 benefits could be reduced by 23-24%. The Committee for a Responsible Federal Budget projects a 24% cut by late 2032 for retirees, equating to an $18,100 annual reduction for a typical dual-earning couple retiring in 2033.

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2024 Update to the OASDI Beneficiaries by State and County

Rick Connor  |  Aug 25, 2025

Almost four years ago I wrote an article about the 2020 OASDI Beneficiaries by State and County report. The report is put out by the Social Security Administration (SSA), and provides a wealth of interesting statistics. Here is the link to the 2024 report where you can investigate detailed national and local data.
Here are some basic numbers for context. As of December 2020, the U.S. population was 329,484,123. Four year later it had grown 3.5%,

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